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【结 构 式】 
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【药物名称】BVT-2733 【化学名称】3-Chloro-2-methyl-N-[4-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]thiazol-2-yl]benzenesulfonamide hydrochloride 【CA登记号】376641-65-5, 376640-41-4 (free base), 376640-42-5 (monotrifluoroacetate) 【 分 子 式 】C17H22Cl2N4O3S2 【 分 子 量 】465.42389 |
【开发单位】Biovitrum (Originator) 【药理作用】Antidiabetic Drugs, ENDOCRINE DRUGS, Type 2 Diabetes Mellitus, Agents for, 11-beta-Hydroxysteroid Dehydrogenase Type 1 (11beta-HSD1) Inhibitors |
合成路线1
Acylation of ethyl 2-amino-4-thiazolylacetate (I) with 3-chloro-2-methylbenzenesulfonyl chloride (II) in pyridine affords sulfonamide (III). After alkaline hydrolysis of the ethyl ester group of (III), the resultant carboxylic acid (IV) is coupled to N-methylpiperazine (V) by means of EDC to furnish the target amide.
| 【1】 Barf, T.; Vallgarda, J.; Emond, R.; Haggstrom, C.; Kurz, G.; Nygren, A.; Larwood, V.; Mosialou, E.; Axelsson, K.; Olsson, R.; Engblom, L.; Edling, N.; Ronquist-Nii, Y.; Ohman, B.; Alberts, P.; Abrahmsen, L.; Arylsulfonamidothiazoles as a new class of potential antidiabetic drugs. Discovery of potent and selective inhibitors of potent and selective inhibitors of the 11beta-hydroxysteroid dehydrogenase type 1. J Med Chem 2002, 45, 18, 3813. |
| 【2】 Emond, R.; Barf, T.; Kurz, G.; Nilsson, M.; Vallgarda, J. (Biovitrum AB); Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1. EP 1283831; WO 0190090 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 61407 | Ethyl 2-amino-4-thiazoleacetate; Ethyl 2-aminothiazole-4-acetate; Ethyl-2-(2-Aminothiazole-4-Yl)acetate; (2-Amino-4-thiazolyl)acetic Acid Ethyl Ester; Ethyl (2-Amino-4-thiazolyl)acetate; Ethyl 2-(2-aminothiazol-4-yl)acetate; Ethyl 2-aminothiazol-4-yl-acetate | 53266-94-7 | C7H10N2O2S | 详情 | 详情 |
| (II) | 61408 | 3-Chloro-2-methylbenzenesulfonyl chloride; 3-Chloro-2-methylbenzenesulphonyl chloride | 80563-86-6 | C7H6Cl2O2S | 详情 | 详情 |
| (III) | 61409 | ethyl 2-(2-{[(3-chloro-2-methylphenyl)sulfonyl]amino}-1,3-thiazol-4-yl)acetate | C14H15ClN2O4S2 | 详情 | 详情 | |
| (IV) | 61410 | 2-(2-{[(3-chloro-2-methylphenyl)sulfonyl]amino}-1,3-thiazol-4-yl)acetic acid | C12H11ClN2O4S2 | 详情 | 详情 | |
| (V) | 10061 | 1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine | 109-01-3 | C5H12N2 | 详情 | 详情 |